1-(1-methyl-1H-indol-3-yl)-3-chloropropan-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(1-methyl-1H-indol-3-yl)-3-chloropropan-1-one
• 英文别名: 3-Chloro-1-(1-methylindol-3-yl)propan-1-one；3-chloro-1-(1-methylindol-3-yl)propan-1-one
• 化学式: C₁₂H₁₂ClNO
• 分子量: 221.686
• InChiKey: YRWVUUSLINGXHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  碘苯 、 1-(1-methyl-1H-indol-3-yl)-3-chloropropan-1-one 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0~90.0 ℃ 、100.0 kPa 条件下， 反应 16.0h， 以85%的产率得到(E)-1-(1-methyl-1H-indol-3-yl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Synthesis of chalcones via domino dehydrochlorination/Pd(OAc)2-catalyzed Heck reaction

  摘要：

  A new method has been developed for the cross-coupling of aryl halides with beta-chloroalkyl aryl ketones and their ester and amide analogs through a domino dehydrochlorination/Pd(OAc)(2)-catalyzed Heck reaction sequence. The enone intermediates generated in situ reduced the occurrence of side reactions and therefore enhanced the efficiency of the reaction. This reaction exhibited good tolerance to various functional groups on both substrates and provides rapid access to a wide range of chalcone derivatives. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s1872-2067(14)60247-3
• 作为产物：
  描述：

  1-甲基吲哚 、 3-氯丙酰氯 在 二甲基氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以65%的产率得到1-(1-methyl-1H-indol-3-yl)-3-chloropropan-1-one
  参考文献：
  名称：

  铑（I）通过多米诺脱氢/共轭加成反应催化β-氯代酮及其相关衍生物的芳构化

  摘要：

  β-氯酮及其酯和酰胺衍生物的高效芳基化是通过多米诺脱氢/ Rh（I）催化的共轭物加成反应实现的。原位生成的乙烯基酮及其类似物被鉴定为反应中间体。本合成方案为（手性）β-芳基酮，酯和酰胺提供了一条简明的途径。

  DOI：

  10.1002/adsc.201200821

文献信息

• Copper-Catalyzed Tandem Asymmetric Borylation of β-Chloroalkyl Aryl Ketones and Related Compounds
  作者：Quanbin Jiang、Tenglong Guo、Zhengkun Yu

  DOI：10.1002/cctc.201402823

  日期：2015.2

  The Cu‐catalyzed, one‐pot tandem (asymmetric) borylation of β‐chloroalkyl aryl ketones via the in situ generated acyclic enones with bis(pinacolato)diboron was achieved efficiently to reach up to 97 % yield and 99 % enantioselectivity for the formal sp3 CCl borylation products. The present methodology provides an efficient alternative route to (chiral) alkylboron compounds.

  通过原位生成的无环烯酮与双（频哪醇）二硼烷进行Cu催化的一锅串联（不对称）β-氯烷基芳基酮的硼化反应，可以有效地实现形式sp的高达97％的收率和99％的对映选择性3种ç 氯硼基化产品。本方法为（手性）烷基硼化合物提供了有效的替代途径。
• Synthesis of chalcones via domino dehydrochlorination/Pd(OAc)2-catalyzed Heck reaction
  作者：Tenglong Guo、Quanbin Jiang、Likun Yu、Zhengkun Yu

  DOI：10.1016/s1872-2067(14)60247-3

  日期：2015.1

  A new method has been developed for the cross-coupling of aryl halides with beta-chloroalkyl aryl ketones and their ester and amide analogs through a domino dehydrochlorination/Pd(OAc)(2)-catalyzed Heck reaction sequence. The enone intermediates generated in situ reduced the occurrence of side reactions and therefore enhanced the efficiency of the reaction. This reaction exhibited good tolerance to various functional groups on both substrates and provides rapid access to a wide range of chalcone derivatives. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.
• Rhodium(I)-Catalyzed Arylation of β-Chloro Ketones and Related Derivatives through Domino Dehydrochlorination/ Conjugate Addition
  作者：Quanbin Jiang、Tenglong Guo、Qingfu Wang、Ping Wu、Zhengkun Yu

  DOI：10.1002/adsc.201200821

  日期：2013.6.17

  Highly efficient arylations of β‐chloro ketones and their ester and amide derivatives were achieved by means of domino dehydrochlorination/Rh(I)‐catalyzed conjugate addition. In situ generated vinyl ketones and their analogues were identified as the reaction intermediates. The present synthetic protocol provides a concise route to (chiral) β‐aryl ketones, esters, and amides.

  β-氯酮及其酯和酰胺衍生物的高效芳基化是通过多米诺脱氢/ Rh（I）催化的共轭物加成反应实现的。原位生成的乙烯基酮及其类似物被鉴定为反应中间体。本合成方案为（手性）β-芳基酮，酯和酰胺提供了一条简明的途径。